EP0550107B1 - Long-chain ketene dimers - Google Patents
Long-chain ketene dimers Download PDFInfo
- Publication number
- EP0550107B1 EP0550107B1 EP92204040A EP92204040A EP0550107B1 EP 0550107 B1 EP0550107 B1 EP 0550107B1 EP 92204040 A EP92204040 A EP 92204040A EP 92204040 A EP92204040 A EP 92204040A EP 0550107 B1 EP0550107 B1 EP 0550107B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- triethyl amine
- continuous operation
- reaction
- process according
- triethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002561 ketenes Chemical class 0.000 title claims abstract description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 111
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229940086542 triethylamine Drugs 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- -1 carboxylic acid chlorides Chemical class 0.000 claims description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000004513 sizing Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 238000011049 filling Methods 0.000 description 7
- 230000001105 regulatory effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/87—Preparation of ketenes or dimeric ketenes
- C07C45/89—Preparation of ketenes or dimeric ketenes from carboxylic acids, their anhydrides, esters or halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/88—Ketenes; Dimeric ketenes
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/17—Ketenes, e.g. ketene dimers
Definitions
- the invention relates to long-chain ketene dimers deriving from saturated or unsaturated carboxylic acids and in particular to a process for the preparation of same.
- Ketenes can be perceived as inner anhydrides of carboxylic acids. Most ketenes dimerise or are stable only as dimers, such as the ketenes which derive from higher fatty acids.
- these ketene dimers are prepared by reacting corresponding carboxylic acid chlorides with tertiary amines, more particularly triethyl amine.
- the course of reaction as represented for example by the reaction of lauric acid chloride with triethyl amine, may be depicted as follows.
- the intermediarily formed ketene immediately dimerises into a diketene.
- the amine can be recovered from the amine hydrochloride formed as by-product by mixing an aqueous solution of the hydrochloride with sodium hydroxide solution and separating the organic phase which forms.
- DE-OS 2 327 988 discloses a process in which the amine hydrochloride is separated by briefly washing it with a diluted solution of neutral salt, e.g. with a 10% solution of sodium sulphate.
- a diluted solution of neutral salt e.g. with a 10% solution of sodium sulphate.
- sodium sulphate means the introduction into the process of a further chemical substance, which likewise must be worked up again or disposed of.
- DE-OS 2 927 118 recommends carrying out the conversion of the fatty acid chloride with a mixture of trimethyl amine and some other tertiary amine.
- DE-OS 2 927 118 recommends carrying out the conversion of the fatty acid chloride with a mixture of trimethyl amine and some other tertiary amine.
- this process also requires inert solvents to control the viscosity of the intermediate product.
- this process is also attended with the drawbacks already mentioned above because use has to be made of organic solvents.
- DE-OS 3 434 212 does not describe an essentially different process either, since instead of the otherwise used organic solvent it employs melted wax, which, ultimately, is likewise an organic solvent. Admittedly, this wax does not have to be removed, since it can be used together with the diketene in special paper sizing processes. However, it is not possible to prepare diketenes in the pure form according to this process.
- the carboxylic acid chloride is fed into the recipient at a rate of not more than 1 mole/hour per mole of present triethyl amine.
- an after-reaction time may be adhered to, e.g. of 5 to 30 minutes, more particularly 10-20 minutes.
- the conversion is conveniently carried out at a temperature in the range of 50° to 100°C, more particularly in the range of 55°-65°C.
- the treatment of the reaction mixture is best carried out with an aqueous solution containing 0-50 wt.% of triethyl amine hydrochloride and 3-32 wt.%, preferably 4-6 wt.%, of hydrochloric acid.
- the separation of the aqueous phase from the ketene can take place, int. al., through sedimentation or centrifuging.
- the obtained ketene may be dried by means of countercurrent drying, e.g. with dry nitrogen.
- the amine hydrochloride may be treated in a conventional manner with, say, sodium hydroxide solution to recover the amine.
- the process according to the invention is carried out continuously, with the starting components being continuously fed into an agitator vessel or a loop reactor for carrying out the main reaction, and the after-reaction being carried out in a tubular reactor connected thereto at the outlet side.
- a vessel equipped with an effective stirrer and internal and external heat exchangers is provided to carry out the process according to the invention.
- inlets for the separate dosing of the starting substances an outlet for discharging the reaction mixture and devices for measuring the existing temperature, pressure, and viscosity.
- a highly effective stirrer adapted to the mixing problem such as an appropriately constructed anchor agitator, in order to ensure sufficient backmixing in the reaction medium and heat transfer ratios for the discharge of the enthalpy of reaction.
- the reaction mixture composed of triethyl amine, triethyl amine hydrochloride, and ketene dimer is treated with diluted aqueous hydrochloric acid or an aqueous solution of hydrochloric acid and triethyl amine hydrochloride to neutralise the excess amine and extract the crystalline product TEA.HCl from the mixing phase.
- the reaction mixture is poured into the acid solution or the acid salt solution with stirring.
- the amount of hydrochloric acid used is as much as is required to remain always in the acid pH range of the aqueous solution.
- the obtained ketene is free of residues of organic solvent and contains only a minor quantity of product-typical impurities such as fatty acid anhydrides and fatty acids.
- the separation of the ketene dimer and the further working up/purification thereof can be carried out in a simple manner.
- a cylindrical agitator vessel with thermostatable jacket and an effective capacity of 1 l ( ⁇ x h: 10 * 14 cm) was equipped with an anchor agitator reaching to the inner wall.
- the anchor agitator in its typical design covers the entire bottom surface and the whole 14 cm cylinder height of the reaction apparatus.
- a thermometer attached at half the inner radius a continuously functioning feeding device for organic acid chlorides in the agitator vessel, and a reflux condenser with superimposed Bunsen valve.
- a commercially available 2 kW circulation thermostat with a liquid volume of 5 l and an external heat exchanger.
- the transport of the heat carrier medium between the thermostat and the double jacket of the reaction vessel was effected via the thermostat's internal pump.
- TEA triethyl amine
- TEA*HCl triethyl amine hydrochloride
- the treatment of the crude product described hereinbelow may serve either to obtain a sample for analytical characterisation, or as a basis for scaled-up separation and purification operations.
- the organic fat phase was then transferred to a round-bottom flask and dried in a rotation evaporator at 65°C under water jet vacuum for 15-30 minutes. A drying loss of 1,02 g (0,76 wt.%) was obtained as a result of the removal of water. The drying process can be speeded up considerably by passing through dry nitrogen.
- the amine salt crystallised out through the removal of water and still containing AKD can then be removed by means of suitable filtration steps. In this way 0,95 g TEA*HCl (0,71 wt.%) were separated.
- the proportion of AKD contained in the product was determined in a known manner by means of morpholine titration and adjusted to the free fatty acid content. As a further characteristic magnitude the acid number, which was determined in accordance with ASTM D 974-64, was taken into consideration.
- the AKD wax characterised by these methods had an AKD content of 90,5% and an acid number of 7 mg KOH/g.
- Example 2 Preparation of AKD in continuous operation with a two-step agitator vessel cascade
- An agitator vessel (1 l) constructed and dimensioned as in Example 1 was connected in cascade with a similar apparatus with an effective capacity of 250 ml.
- stirrer in the second cascade reactor was used an anchor agitator of the same design and arrangement but adapted to the spatial conditions.
- the two reactors had a double-jacket construction, and were connected in series for heating and cooling.
- installed at half the inner radius of the reactors were an internal thermometer and a continuously functioning feeding device for organic acid chlorides and triethyl amine, respectively, and a reflux condenser with superimposed Bunsen valve.
- the reactant use was made of a commercially available 2 kW circulation thermostat with a liquid volume of 5 l and an external heat exchanger. The transport of the heat carrier medium between the thermostat and the double jacket of the reaction vessel was effected via the thermostat's internal pump.
- the required transport of substance between the two cascade vessels takes place via a controllable gear pump kept at 60°C.
- the discharge from the second vessel is so controlled by the appropriate setting of the bottom discharge valve that the filling level was kept at its designated height.
- 230,1 g (2,27 moles) of TEA were charged into the first cascade vessel and brought to a reaction temperature of 60°C. After the rotational speed of the stirrer had been set at 300 rpm, the dosing was started, as in Example 1, of 614,3 g (2,08 moles) of FAC, the rate of feeding being so regulated that the indicated amount was completely transferred to the first reactor in 60 minutes. Immediately on conclusion of the single feeding of FAC, the dosing of TEA to the first reactor was connected up and so regulated, that within 60 minutes 230,9 g (2,28 moles) of TEA were passed to the reactor.
- the (rising) liquid level was then kept at its nominal level by appropriate setting of the gear pump and dosing to the second reactor.
- its bottom valve remained closed in the starting phase and only after the nominal filling level of 250 ml at 60°C had been reached was it opened so far as to give an equilibrium condition.
- An AKD wax obtained according to this example had an AKD content of 91,5% and an acid number of 10 mg KOH/g.
- Example 3 Preparation of AKD in continuous operation with a cascade composed of a loop reactor and an agitator vessel
- An agitator vessel constructed and dimensioned as in Example 2 (1 l) (cascade vessel no. 1) was connected in series with a laminar driven tubular reactor with an effective capacity of 375 ml ( ⁇ internally 9 mm).
- the tubular reactor had a double-jacket construction and was connected in series with the double jacket of the agitator vessel for thermostating. To maintain the nominal filling level in the agitator vessel the reactors were effectively mutually disconnected by means of a controllable gear pump.
- the outlet of the tubular reactor was provided with a small swan neck to prevent it from emptying.
- 230,1 g (2,27 moles) of TEA were charged into the agitator vessel and brought to a reaction temperature of 60°C.
- the dosing was started of 614,3 g (2,08 moles) of FAC, the rate of feeding being so regulated that the indicated amount was passed to the agitator vessel in 60 minutes.
- the dosing of TEA to the first reactor was connected up and so regulated, that within 60 minutes 230,9 g (2,27 moles) of TEA were passed to the reactor.
- the liquid level in the vessel was then kept at its nominal level by appropriate setting of the gear pump and dosing to the connected tubular reactor.
- An AKD wax obtained according to this example had an AKD content of 92,5% and an acid number of 6 mg KOH/g.
- Example 4 Preparation of AKD in continuous operation using a loop reactor and a tubular reactor connected in series
- reaction loop of 380 ml ( ⁇ internally 11 mm) overall content equipped with a gear pump for circulating the reaction product and two spatially separated static mixers on the pressure side for homogeneous feeding of the reactants (FAC follows TEA).
- the reaction temperature was controlled by means of two PT100 detecting elements, which in each case were arranged upstream and downstream of the static mixers.
- the loop branched out in a laminar driven tubular reactor with an effective capacity of 375 ml ( ⁇ internally 9 mm). Steps to disconnect pressure between the reactors, e.g. by means of regulating valves or forced feeding devices, did not prove necessary in this method of operation.
- the reactants FAC and TEA were made available from storage containers and separately dosed into the loop for the respective static mixer via feed pumps.
- the two reaction devices had a double jacket construction and were connected in series for thermostating by means of a circulation thermostat.
- the outlet of the tubular reactor was provided with a small swan neck to prevent emptying.
- the loop was first filled completely with fresh AKD. This was conveniently done by taking melted AKD wax from a storage container and pumping it around the loop until bubbles were no longer to be determined therein. The AKD storage container was then disconnected and the circulation pumping of the AKD continued until the required reaction temperature of 60°C had reached its state of equilibrium. Finally, the volume flow in the loop was set at 100 kg/hour or - taking into account the density of 860 kg/m3 of the mixture of AKD and TEA-HCl - at 116 l/hour.
- An AKD wax obtained according to this example had an AKD content of 91,5% and an acid number of 8 mg KOH/g.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Steroid Compounds (AREA)
- Forklifts And Lifting Vehicles (AREA)
- Devices For Conveying Motion By Means Of Endless Flexible Members (AREA)
- Warehouses Or Storage Devices (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP91203425 | 1991-12-30 | ||
EP91203425 | 1991-12-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0550107A1 EP0550107A1 (en) | 1993-07-07 |
EP0550107B1 true EP0550107B1 (en) | 1996-01-31 |
Family
ID=8208115
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92204040A Expired - Lifetime EP0550107B1 (en) | 1991-12-30 | 1992-12-21 | Long-chain ketene dimers |
Country Status (9)
Country | Link |
---|---|
US (1) | US5344943A (no) |
EP (1) | EP0550107B1 (no) |
JP (1) | JP2980475B2 (no) |
AT (1) | ATE133648T1 (no) |
CA (1) | CA2086452C (no) |
DE (1) | DE69208071T2 (no) |
ES (1) | ES2083076T3 (no) |
FI (1) | FI106195B (no) |
NO (1) | NO179170C (no) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105541760B (zh) * | 2016-01-15 | 2018-02-13 | 苏州天马精细化学品股份有限公司 | 一种液体akd蜡的制备方法 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE171744T1 (de) * | 1993-02-15 | 1998-10-15 | Eka Chemicals Ab | Verfahren zur verminderung des gehalts an organischen lösungsmitteln in cellulose-reaktiven wasserabweisenden mitteln |
SE9300584D0 (sv) * | 1993-02-22 | 1993-02-22 | Eka Nobel Ab | A process for the production of ketene dimers |
SE511318C2 (sv) * | 1993-02-22 | 1999-09-13 | Eka Chemicals Ab | Förfarande för framställning av ketendimerer |
GB9309604D0 (en) * | 1993-05-10 | 1993-06-23 | Hercules Inc | Process for the manufacture of alkyl ketene dimer |
US5685815A (en) * | 1994-02-07 | 1997-11-11 | Hercules Incorporated | Process of using paper containing alkaline sizing agents with improved conversion capability |
EP0741121B1 (de) * | 1995-05-03 | 1999-07-14 | BASF Aktiengesellschaft | Verfahren zur Herstellung von lösungsmittelarmen Alkyldiketenen |
FI104714B (fi) * | 1998-12-04 | 2000-03-31 | Neste Oyj | Menetelmä alkyyliketeenidimeerien valmistamiseksi |
DE10158661A1 (de) * | 2001-11-30 | 2003-06-12 | Basf Ag | Verfahren zur Herstellung von Alkylketendimeren |
DE10222624A1 (de) * | 2002-05-17 | 2003-11-27 | Schill & Seilacher | Verfahren zur Herstellung von Dialkyldiketenen |
PT1976817E (pt) | 2006-01-03 | 2011-07-25 | Hercules Inc | Preparação de dímeros de alquil-ceteno |
CN101845030B (zh) * | 2010-01-19 | 2012-10-17 | 苏州天马精细化学品股份有限公司 | 连续化制备akd的方法 |
CN102962026B (zh) * | 2012-12-04 | 2014-02-05 | 苏州天马精细化学品股份有限公司 | 连续化无溶剂制备高纯度akd的设备及方法 |
CN103102333B (zh) * | 2013-01-25 | 2015-01-21 | 甘肃银光聚银化工有限公司 | 一种烷基烯酮二聚物的生产方法 |
CN112321540B (zh) * | 2019-08-05 | 2021-09-24 | 丰益表面活性材料(连云港)有限公司 | 制备烷基烯酮二聚体的方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0437764A1 (de) * | 1990-01-18 | 1991-07-24 | BASF Aktiengesellschaft | Stabilisierte wässrige Alkyldiketenemulsionen |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE748980C (de) * | 1937-12-03 | 1944-12-19 | Verfahren zur Herstellung von hoehermolekularen Ketenen | |
US2369919A (en) * | 1938-10-13 | 1945-02-20 | Du Pont | Ketoethenones and process therefor |
DE2327988A1 (de) * | 1973-06-01 | 1975-01-02 | Henkel & Cie Gmbh | Verfahren zur herstellung laengerkettiger dimerer alkylketene |
DE2335488A1 (de) * | 1973-07-12 | 1975-02-06 | Basf Ag | Verfahren zur herstellung von fettalkyldiketenen |
DE2927118C2 (de) * | 1979-07-05 | 1981-10-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Fettalkyldiketenen |
DE3434212A1 (de) * | 1984-09-18 | 1986-03-20 | Schill & Seilacher GmbH & Co, 7030 Böblingen | Verfahren zur herstellung von ketendimeren und deren verwendung |
JPH0436258A (ja) * | 1990-05-29 | 1992-02-06 | Nippon Oil & Fats Co Ltd | アルキルケテンダイマーの製造法 |
-
1992
- 1992-12-21 EP EP92204040A patent/EP0550107B1/en not_active Expired - Lifetime
- 1992-12-21 AT AT92204040T patent/ATE133648T1/de not_active IP Right Cessation
- 1992-12-21 ES ES92204040T patent/ES2083076T3/es not_active Expired - Lifetime
- 1992-12-21 DE DE69208071T patent/DE69208071T2/de not_active Expired - Fee Related
- 1992-12-22 NO NO924984A patent/NO179170C/no not_active IP Right Cessation
- 1992-12-29 US US07/998,810 patent/US5344943A/en not_active Expired - Lifetime
- 1992-12-30 FI FI925950A patent/FI106195B/fi active
- 1992-12-30 CA CA002086452A patent/CA2086452C/en not_active Expired - Fee Related
-
1993
- 1993-01-04 JP JP5015832A patent/JP2980475B2/ja not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0437764A1 (de) * | 1990-01-18 | 1991-07-24 | BASF Aktiengesellschaft | Stabilisierte wässrige Alkyldiketenemulsionen |
Non-Patent Citations (1)
Title |
---|
Ullmann's Encyclopedia, 5th rev. edn., vol. A15, pp. 72/73 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105541760B (zh) * | 2016-01-15 | 2018-02-13 | 苏州天马精细化学品股份有限公司 | 一种液体akd蜡的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
FI106195B (fi) | 2000-12-15 |
FI925950A (fi) | 1993-07-01 |
DE69208071T2 (de) | 1996-08-29 |
CA2086452C (en) | 1999-05-18 |
JPH05271212A (ja) | 1993-10-19 |
JP2980475B2 (ja) | 1999-11-22 |
NO924984L (no) | 1993-07-01 |
CA2086452A1 (en) | 1993-07-01 |
FI925950A0 (fi) | 1992-12-30 |
ES2083076T3 (es) | 1996-04-01 |
ATE133648T1 (de) | 1996-02-15 |
DE69208071D1 (de) | 1996-03-14 |
EP0550107A1 (en) | 1993-07-07 |
NO179170B (no) | 1996-05-13 |
US5344943A (en) | 1994-09-06 |
NO179170C (no) | 1996-08-21 |
NO924984D0 (no) | 1992-12-22 |
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